DE2142354A1 - Anthraquinone compounds that are poorly soluble in water, their preparation and use - Google Patents
Anthraquinone compounds that are poorly soluble in water, their preparation and useInfo
- Publication number
- DE2142354A1 DE2142354A1 DE19712142354 DE2142354A DE2142354A1 DE 2142354 A1 DE2142354 A1 DE 2142354A1 DE 19712142354 DE19712142354 DE 19712142354 DE 2142354 A DE2142354 A DE 2142354A DE 2142354 A1 DE2142354 A1 DE 2142354A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- carbon atoms
- substituents
- parts
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 Anthraquinone compounds Chemical class 0.000 title claims description 19
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 9
- 239000000975 dye Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000004043 dyeing Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 2
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- NQGXOOJUAKCSLM-UHFFFAOYSA-N 2-phenoxyanthracene-9,10-dione Chemical compound C=1C=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=1OC1=CC=CC=C1 NQGXOOJUAKCSLM-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- LTWUOCPXESHRBG-UHFFFAOYSA-N N-(9,10-dioxoanthracen-1-yl)-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O LTWUOCPXESHRBG-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 229920001577 copolymer Chemical class 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080236 sodium cetyl sulfate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
- C09B1/545—Anthraquinones with aliphatic, cycloaliphatic or araliphatic ether groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
2U23542U2354
PatentnnwclfeiPatentnwclfei
Dr. W. Scheut. V pl.-Ιπα. P. Wirth Dr. W. Scheut. V pl.-Ιπα. P. Wirth
Dip! !no ,'1. ;.·ο , ν - WgDip! ! no, '1. ;. Ο, ν - Wg
Dr. V. £.:-.-:.■».. :'^v/cri;ik Dr. V. £.: -.- :. ■ »..: '^ v / cri; ik
D:. P. Weirihoio, Or. D. Gudel D :. P. Weirihoio, Or. D. Gudel
'< Frankfurt/M., Gr. Eschenheimer Str. 3Ä'<Frankfurt / M., Gr. Eschenheimer Str. 3Ä
J.ÄNDUZ ΑΘJ.ÄNDUZ ΑΘ
ri/3h;,b case 150-3202ri / 3h;, b case 150-3202
In Wasser schwer lösliche Anthrachinonverbindungen, ihre Herstellung und Verwendung.Anthraquinone compounds that are sparingly soluble in water, their manufacture and use.
Gegenstand der Erfindung sind in Wasser schwer lösliche l~Amino-2-alkoxy-4-arylsulfonylamino-anthrachinonverbindungen, die sich hervorragend als Dispersionsfarbstoffe, zum Färben oder Bedrucken von Fasern oder Fäden oder daraus hergestellten Materialien aus voll- oder halbsynthetischen, hydrophoben, hochmolekularen organischen Stoffen eignen. Die mit diesen neuen Farbstoffen erhaltenen Färbungen zeichnen sich insbesondere durch ihre Sublimier- und Lichtechtheit aus.The invention relates to l ~ amino-2-alkoxy-4-arylsulfonylamino-anthraquinone compounds that are sparingly soluble in water, which are excellent as disperse dyes, for dyeing or printing fibers or threads or made from them Materials made from fully or semi-synthetic, hydrophobic, high-molecular organic substances are suitable. the The dyeings obtained with these new dyes are distinguished in particular by their fastness to sublimation and light the end.
209810/1658209810/1658
2U23542U2354
Die neuen Anthrachinonverbindungen entsprechen der FormelThe new anthraquinone compounds correspond to the formula
ji0
ji
0 Il
0
I 2 NH-
I 2
(D.(D.
können.can.
worin R1 Alkylen mit bis zu 4 Kohlenstoffatomen,wherein R 1 is alkylene with up to 4 carbon atoms,
R_ Alkoxy mit 3, 4, 5 oder 6 Kohlenstoffatomen, Cycloalkoxy, Aryloxy, Äcyloxy, Hydroxyalkoxy, Halogenalkoxy, Cyanalkoxy, Alkoxyalkoxy oder ArylalkoxyR_ alkoxy with 3, 4, 5 or 6 carbon atoms, Cycloalkoxy, aryloxy, acyloxy, hydroxyalkoxy, Haloalkoxy, cyanoalkoxy, alkoxyalkoxy or arylalkoxy
und R_ Aryl bedeuten,and R_ mean aryl,
wobei die Alkyl- und Arylreste sowie der Kern A weitere Substituenten mit Ausnahme von Sulfonsäuregruppen tragenwhere the alkyl and aryl radicals and the core A carry further substituents with the exception of sulfonic acid groups
Unter Alkylen (R.) sind sowhol geradkettige als auch verzweigte Radikale zu verstehen. Aryl, auch in Aryloxy oder Arylalkoxy bedeutet vorzugsweise Phenyl, das zum Beispiel Halogen, worunter insbesondere Fluor, Chlor oder Brom zu verstehen ist, Hydroxyl, Alkyl, Alkoxy, Cyan, Rhodan, Nitro, Trifluormethyl, Acyl, Acyloxy, Acylamino, Amino, Alkylamino, Arylamino, Phenyl, Phenyloxy, Alkyimercapto oder Phenylmercapto als Substituenten tragen kann. Unter CycloalkoxyAlkylene (R.) includes both straight-chain and branched ones Understand radicals. Aryl, also in aryloxy or arylalkoxy, is preferably phenyl, for example Halogen, which means in particular fluorine, chlorine or bromine, hydroxyl, alkyl, alkoxy, cyano, rhodan, nitro, Trifluoromethyl, acyl, acyloxy, acylamino, amino, alkylamino, Arylamino, phenyl, phenyloxy, alkyimercapto or phenylmercapto can carry as substituents. Under cycloalkoxy
209810/1658209810/1658
2U23542U2354
ist vor allera Cyc3 ohexyloxy zu verstehen. Sofern nicht anders präzisiert, bedeutet Alkyl bzw. Alkoxy immer eine Gruppe die 1, 2, 3 oder 4 Kohlenstoffatome enthält, oder Cyclohexyl. Unter den Substituenten die an die Alkyl- oder Alkoxyreste gebunden sein können, sind besonders Halogen, insbesondere Chlor und Brom, Hydroxyl, Alkoxy, Cyan, Rhodan, Nitro, Acyl, Acyloxy, Acylamino, Phenyl und Phenyloxy zu erwähnen.is to be understood above all Cyc3 ohexyloxy. Unless otherwise More precisely, alkyl or alkoxy always means a group that contains 1, 2, 3 or 4 carbon atoms, or cyclohexyl. Among the substituents, those on the alkyl or alkoxy radicals can be bonded are especially halogen, especially chlorine and bromine, hydroxyl, alkoxy, cyano, rhodan, nitro, acyl, Mention should be made of acyloxy, acylamino, phenyl and phenyloxy.
Bevorzugte Äcylgruppen entsprechen der Formel R—Y— oder R'-Z-Preferred acyl groups correspond to the formula R — Y— or R'-Z-
darin bedeutenmean in it
R einen Kohlenwasserstoffrest, der die oben angeführten Substituenten tragen und/oder Heteroatome enthalten kann, vorzugsweise einen Alkyl- oder Phenylrest,R is a hydrocarbon radical that corresponds to those listed above Can carry substituents and / or contain heteroatoms, preferably an alkyl or Phenyl radical,
Y ein Radikal -0-CO- oder -SO«-, R* ein Wasserstoffatom oder R, Z ein Radikal -CO-, -MR11CO- oder -NR11SO- und R" ein Wasserstoff atom oder R.Y is a radical -0-CO- or -SO «-, R * is a hydrogen atom or R, Z is a radical -CO-, -MR 11 CO- or -NR 11 SO- and R" is a hydrogen atom or R.
Die Herstellung der neuen Verbindungen der Formel (I) erfolgt durch Kondensation einer Anthrachinonverbindung der FormelThe new compounds of the formula (I) are prepared by condensation of an anthraquinone compound of the formula
209810/1658209810/1658
2U23542U2354
O NH,O NH,
(II),(II),
worin X einen austauschbaren Substituenten, z.B. Alkoxy oder Aryloxy, vorzugsweise jedoch ein Halogenatom, insbesondere ein Chlor- oder Bromatom, oder eine SuIfonsäuregruppe bedeutet,wherein X is an exchangeable substituent, e.g., alkoxy or aryloxy, but preferably a halogen atom, in particular a chlorine or bromine atom, or means a sulfonic acid group,
mit einer Verbindung der Formelwith a compound of the formula
HO—R1-HO — R 1 -
in Gegenwart von säurebindenden Mitteln.in the presence of acid-binding agents.
(III)(III)
Die Kondensation findet im allgemeinen bei Temperaturen zwischen 100° und 1800C statt. Meist arbeitet man in einem Ueberschuss der Verbindung der Formel (III), die in diesem Fall als Lösungsmittel wirkt, es können jedoch gegebenenfalls auch andere inerte Lösungsmittel zugegen sein, z.B. Xylole, Chlorbenzole oder Nitrobenzol. Als säurebindende Mittel kommen z.B. Alkalihydroxide insbesondere Kaliumoder Natri\imhydroxid, aber auch Calciumhydroxid oder Magnesiumoxid, Natriumcarbonat oder Natriumbicarbonat, in Betracht, Die entstandenen Verbindungen der Formel (I) können nach erfolgter Reaktion beim Abkühlen als Niederschlag durch Abfil-The condensation generally takes place at temperatures between 100 ° and 180 0 C. In most cases, an excess of the compound of the formula (III), which in this case acts as a solvent, is used, but other inert solvents may also be present, for example xylenes, chlorobenzenes or nitrobenzene. Suitable acid-binding agents are, for example, alkali hydroxides, in particular potassium or sodium hydroxide, but also calcium hydroxide or magnesium oxide, sodium carbonate or sodium bicarbonate.
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trieren oder auch durch Eindampfen des Lösungsmittels im Vakuum gewonnen werden.trieren or by evaporation of the solvent in the Vacuum can be obtained.
Die bevorzugten Farbstoffe entsprechen der FormelThe preferred dyes correspond to the formula
(IV),(IV),
worin R- unsubstituiertes Phenyl oder Phenyl das Methyl, Methoxy, Aethoxy, Chlor, Brom oder Nitro als Substituenten trägtwhere R- unsubstituted phenyl or phenyl is methyl, Methoxy, ethoxy, chlorine, bromine or nitro carries as substituents
und R eine Älkylgruppe mit 2, 3 oder 4 Kohlenstoffatomen, die Hydroxyäthoxy, Hydroxypropoxy, Methoxyäthoxy, Aethoxyäthoxy, Cyanäthoxy, Cyclohexyloxy, Phenoxy, Benzyloxy, Formyloxy, Acetoxy, Propionyloxy, Butyryloxy oder Benzoyloxy als Substituenten trägt, bedeuten.and R is an alkyl group with 2, 3 or 4 carbon atoms, the hydroxyethoxy, hydroxypropoxy, methoxyethoxy, Ethoxyethoxy, cyanoethoxy, cyclohexyloxy, phenoxy, Benzyloxy, formyloxy, acetoxy, propionyloxy, Bears butyryloxy or benzoyloxy as substituents.
Es ist besonders vorteilhaft, die neuen Farbstoffe vor ihrer Verwendung in Färbepräparate überzuführen. Die Verarbeitung zu Färbepräparaten erfolgt auf allgemein bekannte Weise z.B. durch Mahlen in Gegenwart von Dispergier- und/oder Füllmitteln. Mit den gegebenenfalls im Vakuum oder durch Zerstäuben getrockneten Präparaten kann man, nach Zugabe von mehr oderIt is especially beneficial to use the new dyes before their Use to be converted into dye preparations. The processing into dye preparations is carried out in a generally known manner, e.g. by grinding in the presence of dispersants and / or fillers. With the optionally in a vacuum or by atomization dried preparations can, after adding more or
209810/1058209810/1058
weniger Wasser in sogenannter langer oder kurzer Flotte färben, klotzen oder bedrucken.dye, pad or print less water in so-called long or short liquors.
Die Farbstoffe ziehen aus wässriger Suspension ausgezeichnet auf Textilmaterial aus vollsynthetischen oder halbsynthetischen, hydrophoben, hochmolekularen organischsn Stoffen auf. ψ Besonders geeignet sind sie zum Färben' oder Bedrucken von Textilmaterial aus linearen, aromatischen Polyestern, sowie aus Cellulose 2 1/2-acetat, Cellulosetriacetat und synthetischen Polyamiden. Auch Polyolefine lassen sich mit ihnen färben.The dyes are extremely well absorbed from aqueous suspension on textile material made of fully synthetic or semi-synthetic, hydrophobic, high-molecular organic substances. ψ They are particularly suitable for dyeing or printing textile material made of linear, aromatic polyesters, as well as cellulose 2 1/2 acetate, cellulose triacetate and synthetic polyamides. They can also be used to color polyolefins.
Man färbt, klotzt oder bedruckt nach an sich bekannten, z.B. dem in der französischen Patentschrift Kr. 1.445.371 beschriebenen Verfahren.It is colored, padded or printed according to known methods, e.g. that described in the French patent specification Kr. 1.445.371 Procedure.
™ Die erhaltenen Färbungen besitzen ausgezeichnete Allgemeinechtheiten; hervorzuheben sind die Lichtechtheit, die Thermofixierechtheit, Sublimier- und Plissierechtheit. Sie sind hervorragend nassecht, z.B. wasser-, meerwasser-, wasch- und schweissecht, lösungsmittelecht, insbesondere trockenreinigungsecht, schmälzmittel-, reib-, überfärbe-, ozon-, rauchgas- und chlorecht j sie sind äusserst beständig gegen die Einwirkung der verschiedenen" Permanentpressverfahren und der sogenannten "Soil Release"-Ausrüstungen. Die Reduktionsbe-™ The dyeings obtained have excellent all-round fastness properties; to be emphasized are the light fastness, the heat-setting fastness, the sublimation and pleating fastness. they are excellent wet fast, e.g. water, sea water, washing and perspiration fast, solvent fast, especially dry cleaning fast, lubricant, rubbing, dyeing, ozone, flue gas and chlorine law j they are extremely resistant to the Effect of the various "permanent pressing processes" and the so-called "soil release" equipment.
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ständiglcait (beim Färben */on Po3-\reste-r~Wolle--Mischgewebe) und die Roserve von Wolle und Baumwolle sind gut.constantly lcait (when dyeing * / on Po3- \ reste-r ~ wool - mixed fabrics) and the roserve of wool and cotton are good.
Den aus der ü.S.A.-Patentschrift 3.087.773 und aus der französischen Patentschrift 1.284.003 bekannten, nächstvergleichbaren Farbstoffen sind die hier beanspruchten Farbstoffe in der Sublimierechtheit bzw. im Ziehvermögen überlegen.The one from the ü.S.A. patent specification 3.087.773 and from the French Patent 1,284,003 known, next comparable dyes are the dyes claimed here in superior to sublimation fastness or drawability.
Die in den folgenden Beispielen genannten Teile sind Gewichtsteile, die Temperaturen sind in Celsiusgraden angegeben. The parts mentioned in the following examples are parts by weight, the temperatures are given in degrees Celsius.
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B e i s ρ i e 1 1B e i s ρ i e 1 1
nium r um—mil mil nium r um - mil mil
20 Teile l~AminO"2-phenoxy-4~bensolsu.lfonaraido--anthrachinon20 parts of 1 ~ aminO "2-phenoxy-4 ~ bensol and lfonaraido-anthraquinone
werden rait 5 Teilen Kaliumhydroxid in 100 Teilen Methylearbitol so lange bei 135° gerührt, bis sich dünnschichtchromatographisch kein Ausgangsmaterial mehr nachweisen lässt. Dann wird auf Zimmertemperatur abgekühlt, wobei das Reaktionsprodukt , l-Amino-2-(methoxyäthoxyäthoxy)-4-benzolsulfonamidoanthrachinon, ausfällt. Es wird abfiltriert und mit Methylalkohol und schliesslich mit Wasser gewaschen.are rait 5 parts of potassium hydroxide in 100 parts of methylearbitol Stirred at 135 ° until no more starting material can be detected by thin layer chromatography. then is cooled to room temperature, the reaction product, l-amino-2- (methoxyethoxyethoxy) -4-benzenesulfonamidoanthraquinone, fails. It is filtered off and washed with methyl alcohol and finally with water.
20 Teile des Natriumsalzes von l-Äraino-2-sulfonsäure-4-benzolsulfonamido-anthrachinon werden in 180 Teilen Aethylenglykol-monobutylather in Gegenwart von 5 Teilen Kaliumhydroxid so lange bei 125° gerührt, bis sich kein Ausgangsmaterial mehr nachweisen lässt (Dünnschichtchromatographie). Nach dem Abkühlen werden 5 Teile Eisessig zugesetzt, worauf der auskristallisierte Farbstoff abfiltriert und mit Aethylalkohol und Wasser gewaschen wird.20 parts of the sodium salt of 1-Äraino-2-sulfonic acid-4-benzenesulfonamido-anthraquinone are in 180 parts of ethylene glycol monobutyl ether stirred in the presence of 5 parts of potassium hydroxide at 125 ° until there is no starting material more can be detected (thin layer chromatography). After cooling, 5 parts of glacial acetic acid are added, whereupon it crystallizes out Dye is filtered off and washed with ethyl alcohol and water.
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B e is ρ; i el 3 B ei s ρ; i el 3
20 Teile !-Amino-2-brom-4- (para~methoxybenzolsulfona;nido)~ anthrachinon werden in 100 Teile geschmolzenes Phenylglykol eingetragen und mit 5 Teilen Kaliumhydroxid versetzt. Bei 140° wird nun so lange gerührt bis sich kein Ausgangsmateriai mehr nachweisen lässt. Nach dem Abkühlen wird die Masse auf Wasser ausgeladen und der ausgefallene Farbstoff durch Filtration isoliert.20 parts of! -Amino-2-bromo-4- (para ~ methoxybenzenesulfona; nido) ~ anthraquinone are introduced into 100 parts of molten phenylglycol and mixed with 5 parts of potassium hydroxide. at 140 ° is now stirred until there is no starting material more can be proven. After cooling, the mass becomes discharged onto water and the precipitated dye isolated by filtration.
Ein reineres Produkt wird erhalten, wenn intermediär aus der 2-Halogen-anthrachinonverbindung die 2-Phenoxy-anthrachinonverbindung gebildet und diese mit dem 2-Phenoxyäthanol-l umgesetzt wirdj dies geschieht folgendermassen ι 20 Teile l-Amino-^-brom-^ (para-methoxybenzolsulfonamido) -anthrachinon, 8 Teile Phenol, lOO Teile 2-Phenoxyäthanol und 8 Teile Kaliumcarbonat werden auf oben beschriebene Weise umgesetzt und isoliert.A purer product is obtained, formed when an intermediate from the 2-halo-anthraquinone 2-phenoxy-anthraquinone and these wirdj reacted with the 2-phenoxyethanol-l this follows happens ι 20 parts l-amino - ^ - bromo ^ (para Methoxybenzenesulfonamido) anthraquinone, 8 parts of phenol, 100 parts of 2-phenoxyethanol and 8 parts of potassium carbonate are reacted and isolated in the manner described above.
In der folgenden Tabelle sind die charakteristischen Substituenten von weiteren, erfingungsgemäss herstellbaren Farbstoffen der Formel (IV) angegeben.The following table shows the characteristic substituents of further dyes which can be prepared according to the invention of the formula (IV) indicated.
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2H235A2H235A
Nr.E.g.
No.
ZZ O 3-CH ^ CH ~ -0-CAl-
ZZ O 3
ZZ Zoo -CH 0 CH 0 -O-CH 0 C ^ H 1 .
ZZ zoo
Alle erfindungsgemässen Farbstoffe geben auf Polyesterfasermaterial brillant rote Ausfärbungen.All dyes according to the invention apply to polyester fiber material brilliant red color.
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PLrbebeispiαϊPLrbebeispiαϊ
7 Teile des nacht Beispiel 1 erhaltenen Farbstoffs werden mit 4 Teilen dinaphthyliaethandi sulfonsäuren! Natrium, 4 Teilen Katriumcetylsulfat und 5 Teilen Natriumsulfat in einer Kugelmühle 48 Stunden zu einem feinen Pulver gemahlen. 2 Teile des so erhaltenen Färbepräparats werden in' 3000 Teilen Wasser, welches 3 Teile einer 30-%igen Lösung eines hochsulfonierten Ricinusöls und 20 Teile einer Emulsion eines chlorierten Benzols in Wasser enthält, dispergiert. Bei 20-25° bringt man loO Teile Polyesterfasergewebe ein, erhitzt das Bad in etwa 30 Minuten auf 95 bis 100° und färbt eine Stunde bei 95 bis 100°. Das Färbegut wird aus dem Bad genommen, gespült, 15 Minuten bei 70° mit einer 0,1-1 %igen Lösung eines Alkylph enylpo lyg lylco lather s geseift, nochmals gespült^und getrocknet. Man erhält eine brillant rote Färbung mit ausgezeichneten Echtheiten.7 parts of the dye obtained after Example 1 are mixed with 4 parts of dinaphthyliaethandi sulfonic acids! Sodium, 4 parts Sodium cetyl sulfate and 5 parts of sodium sulfate in a ball mill Ground to a fine powder for 48 hours. 2 parts of the dye preparation obtained in this way are dissolved in 3000 parts of water, which 3 parts of a 30% solution of a highly sulfonated castor oil and 20 parts of an emulsion of a chlorinated benzene contains dispersed in water. At 20-25 ° you bring 100 parts polyester fiber fabric, heats the bath to 95 to 100 ° in about 30 minutes and dyes at 95 to one hour 100 °. The dyed material is taken out of the bath, rinsed, 15 minutes at 70 ° with a 0.1-1% solution of an alkylph enylpo lyg lylco lather s soaped, rinsed again ^ and dried. A brilliant red dyeing with excellent fastness properties is obtained.
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Claims (5)
und R3 Aryl bedeuten,Cycloalkoxy, aryloxy, acyloxy, hydroxyalkoxy, haloalkoxy, cyanoalkoxy, alkoxyalkoxy or arylalkoxy
and R 3 mean aryl,
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1281470A CH534714A (en) | 1970-08-27 | 1970-08-27 | Process for the production of sparingly water-soluble anthraquinone compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2142354A1 true DE2142354A1 (en) | 1972-03-02 |
Family
ID=4386614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712142354 Pending DE2142354A1 (en) | 1970-08-27 | 1971-08-24 | Anthraquinone compounds that are poorly soluble in water, their preparation and use |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE771770A (en) |
| CH (1) | CH534714A (en) |
| DE (1) | DE2142354A1 (en) |
| FR (1) | FR2107068A5 (en) |
| NL (1) | NL7111807A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59168064A (en) * | 1983-03-15 | 1984-09-21 | Sumitomo Chem Co Ltd | Dye for car seat |
-
1970
- 1970-08-27 CH CH1281470A patent/CH534714A/en not_active IP Right Cessation
-
1971
- 1971-08-24 DE DE19712142354 patent/DE2142354A1/en active Pending
- 1971-08-25 FR FR7130793A patent/FR2107068A5/en not_active Expired
- 1971-08-25 BE BE771770A patent/BE771770A/en unknown
- 1971-08-27 NL NL7111807A patent/NL7111807A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59168064A (en) * | 1983-03-15 | 1984-09-21 | Sumitomo Chem Co Ltd | Dye for car seat |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2107068A5 (en) | 1972-05-05 |
| NL7111807A (en) | 1972-02-29 |
| BE771770A (en) | 1971-12-31 |
| CH534714A (en) | 1973-03-15 |
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